A. Hydrogenation of Dienes Using Naphthalene Chromium Tricarbonyl as the Catalyst
Cais et al., "The Catalytic Activity of Tricarbonyl Chromium Complexes of Phenanthrene, Naphthalene and Anthracene in the Hydrogenation of Dienes," Coord. Chem. Rev., Vol. 16, (1975), pages 27-34, discloses kinetic studies on the hydrogenation of dienes using arene chromium tricarbonyls as catalysts, including naphthalene chromium tricarbonyl. The hydrogenation of methyl sorbate, a conjugated diene, was carried out at temperatures ranging from 27.degree. to 120.degree. C. in solvents such as decalin, tetrahydrofuran (THF) and acetone. In addition, naphthalene chromium tricarbonyl was used to catalyze the hydrogenation of 1,4-cyclohexadiene in acetone at a temperature of 40.5.degree. C.; the reaction rate and induction time data suggest that this reaction was extremely sluggish. See also Yagupsky et al., "Solvent-Assisted Regioselective and Stereospecific Hydrogenation of Dienes, at Ambient Temperatures and Pressures Catalyzed by (Naphthalene) Cr(CO).sub.3 ; Nature of the Active Catalytic Species," Inorg. Chim. Acta, Vol. 12, (1975), pages L27-L28, which also discloses the hydrogenation of methyl sorbate at 30.degree. C. and one atmosphere total pressure using naphthalene chromium tricarbonyl as the catalyst.
Eden et al., "Stereospecific and Regioselective Hydrogenation of Bicyclo[2.2.1]Hepta-2,5-Diene and Related Systems Catalyzed by Tricarbonyl Chromium Complexes of Phenanthrene and Naphthalene," Israel J. Chem., Vol. 25, (1977), pp. 223-29, discloses the hydrogenation of norbornadiene and related bicyclic compounds using naphthalene chromium tricarbonyl as the catalyst. Nortricylene was the major product formed (82%) with the minor product being norbornene (18%). This reaction was carried out at a temperature of 30.2.degree. C. in THF.